view:21606 Last Update: 2019-1-30
Parvaneh Pakravan ; Ali Ramazani; Nader Noshiranzadeh ; Alireza Sedrpoushan|
One-Pot Synthesis of Fluorine-Containing Alkenes from In Situ-Generated Stabilized Phosphorus Ylides
Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by 4- (trifluoromethyl)benzyl alcohol leads to vinyltriphenylphosphonium salts, which undergo a Michael addition reaction with a conjugate base to produce the corresponding fluorine-containing stabilized phosphorus ylides. An intermolecular Wittig reaction of the fluorine-containing stabilized phosphorus ylides with ninhydrin leads to the corresponding highly electron-poor fluorine-containing alkenes.